TW393478B - Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl] piperazine - Google Patents
Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl] piperazine Download PDFInfo
- Publication number
- TW393478B TW393478B TW084102592A TW84102592A TW393478B TW 393478 B TW393478 B TW 393478B TW 084102592 A TW084102592 A TW 084102592A TW 84102592 A TW84102592 A TW 84102592A TW 393478 B TW393478 B TW 393478B
- Authority
- TW
- Taiwan
- Prior art keywords
- type
- relative
- measured
- methanesulfonamidoindolyl
- quot
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 23
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 7
- 238000001228 spectrum Methods 0.000 claims abstract description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 15
- 238000011049 filling Methods 0.000 claims description 13
- 125000004889 1-methylethylamino group Chemical group CC(C)N* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 230000002079 cooperative effect Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 230000000704 physical effect Effects 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 229960005319 delavirdine Drugs 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- ZKJKXGCLZUMGNT-UHFFFAOYSA-N methanesulfonic acid;piperazine Chemical compound CS(O)(=O)=O.C1CNCCN1 ZKJKXGCLZUMGNT-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000002002 slurry Substances 0.000 description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241001430294 unidentified retrovirus Species 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RVIXKDRPFPUUOO-UHFFFAOYSA-N dimethylselenide Chemical compound C[Se]C RVIXKDRPFPUUOO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002483 medication Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- -1 1-methylethynyl Chemical group 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 206010020144 Histoplasmosis disseminated Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- FRKDEDBRSLDGIX-UHFFFAOYSA-N methanesulfonate;piperidin-1-ium Chemical compound CS([O-])(=O)=O.C1CC[NH2+]CC1 FRKDEDBRSLDGIX-UHFFFAOYSA-N 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22786094A | 1994-04-15 | 1994-04-15 | |
| US31178094A | 1994-09-23 | 1994-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW393478B true TW393478B (en) | 2000-06-11 |
Family
ID=26921831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW084102592A TW393478B (en) | 1994-04-15 | 1995-03-17 | Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl] piperazine |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6452007B1 (es) |
| EP (1) | EP0755393B1 (es) |
| JP (1) | JP3817261B2 (es) |
| KR (1) | KR100364941B1 (es) |
| CN (1) | CN1147253A (es) |
| AT (1) | ATE207481T1 (es) |
| AU (1) | AU693939B2 (es) |
| CA (1) | CA2184598C (es) |
| CZ (1) | CZ287164B6 (es) |
| DE (1) | DE69523447T2 (es) |
| DK (1) | DK0755393T3 (es) |
| ES (1) | ES2164147T3 (es) |
| FI (1) | FI111364B (es) |
| HU (1) | HU226827B1 (es) |
| IL (1) | IL113162A (es) |
| LV (1) | LV12957B (es) |
| MX (1) | MX9604831A (es) |
| MY (1) | MY116830A (es) |
| NO (1) | NO310024B1 (es) |
| NZ (1) | NZ282211A (es) |
| PL (1) | PL180776B1 (es) |
| PT (1) | PT755393E (es) |
| RU (1) | RU2136677C1 (es) |
| SK (1) | SK282424B6 (es) |
| TW (1) | TW393478B (es) |
| WO (1) | WO1995028398A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6177101B1 (en) | 1998-06-11 | 2001-01-23 | Pharmacia & Upjohn Company | Delavirdine high strength tablet formulation |
| US6872811B1 (en) | 1998-09-30 | 2005-03-29 | Millennium Pharmaceuticals, Inc. | HRPCa9 and HRPCa10 nucleic acids and polypeptides |
| DE102011113749A1 (de) * | 2011-09-14 | 2013-03-14 | Aicuris Gmbh & Co. Kg | Sulfonsäuresalze Heterocyclylamid-substituiertr Imidazole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565924A (en) | 1968-07-01 | 1971-02-23 | Wisconsin Alumni Res Found | 25-hydroxycholfcalciferol |
| US3833622A (en) | 1969-03-17 | 1974-09-03 | Upjohn Co | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
| GB1532682A (en) | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
| IL63968A (en) | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US5563142A (en) * | 1989-12-28 | 1996-10-08 | The Upjohn Company | Diaromatic substituted compounds as anti-HIV-1 agents |
| MX9203454A (es) * | 1989-12-28 | 1992-08-01 | Upjohn Co | Compuestos anti sida diaromaticos substituidos. |
| US5599930A (en) * | 1991-07-03 | 1997-02-04 | The Upjohn Company | Substituted indoles as anti-AIDS pharmaceuticals |
-
1995
- 1995-03-01 PT PT95911842T patent/PT755393E/pt unknown
- 1995-03-01 HU HU9602857A patent/HU226827B1/hu unknown
- 1995-03-01 ES ES95911842T patent/ES2164147T3/es not_active Expired - Lifetime
- 1995-03-01 EP EP95911842A patent/EP0755393B1/en not_active Expired - Lifetime
- 1995-03-01 SK SK1229-96A patent/SK282424B6/sk unknown
- 1995-03-01 JP JP52695295A patent/JP3817261B2/ja not_active Expired - Lifetime
- 1995-03-01 RU RU96119978A patent/RU2136677C1/ru active
- 1995-03-01 CZ CZ19962942A patent/CZ287164B6/cs not_active IP Right Cessation
- 1995-03-01 DK DK95911842T patent/DK0755393T3/da active
- 1995-03-01 CN CN95192523A patent/CN1147253A/zh active Pending
- 1995-03-01 PL PL95316688A patent/PL180776B1/pl unknown
- 1995-03-01 MX MX9604831A patent/MX9604831A/es unknown
- 1995-03-01 KR KR1019960705760A patent/KR100364941B1/ko not_active IP Right Cessation
- 1995-03-01 DE DE69523447T patent/DE69523447T2/de not_active Expired - Lifetime
- 1995-03-01 NZ NZ282211A patent/NZ282211A/en not_active IP Right Cessation
- 1995-03-01 CA CA002184598A patent/CA2184598C/en not_active Expired - Lifetime
- 1995-03-01 US US08/732,254 patent/US6452007B1/en not_active Expired - Lifetime
- 1995-03-01 AU AU35136/95A patent/AU693939B2/en not_active Expired
- 1995-03-01 AT AT95911842T patent/ATE207481T1/de active
- 1995-03-01 WO PCT/US1995/002166 patent/WO1995028398A1/en active IP Right Grant
- 1995-03-17 TW TW084102592A patent/TW393478B/zh not_active IP Right Cessation
- 1995-03-28 IL IL11316295A patent/IL113162A/xx not_active IP Right Cessation
- 1995-03-28 MY MYPI95000766A patent/MY116830A/en unknown
-
1996
- 1996-10-14 FI FI964114A patent/FI111364B/fi not_active IP Right Cessation
- 1996-10-15 NO NO964386A patent/NO310024B1/no not_active IP Right Cessation
-
2002
- 2002-10-24 LV LVP-02-186A patent/LV12957B/en unknown
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